Tetrahedron Letters p. 1865 - 1868 (1987)
Update date:2022-08-16
Topics:
Mash, Eugene A.
Nelson, Keith A.
Heidt, Philip C.
A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal but possessing different dioxolane appendages was prepared and subjected to Simmons-Smith cyclopropanation.The observed diastereoselectivity decreased when oxygen was present in the appendages.In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality.The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.
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